Issa Rae Continues Her Winning Style Evolution

Welcome to "Who Won Fashion Today," where we award the boldest, best dressed person of the day. Winning fashion doesn't necessarily mean you're wearing the most expensive, trendiest, or prettiest dress. Rather, we reward risk-takers—those that stay true to their personal style and make us go, "Now THAT is a LEWK.”

What does it take to stand out at one of the most star-studded events of the calendar year? Ask Issa Rae.

The Insecure actress, who once favored leather jackets and tees, arrived to Essence's Black Women in Hollywood event yesterday in a truly glamorous gown by Francesca Miranda. One that we undoubtedly can add to our beloved Naked Dress gallery.